Proactive assistant
Proactive check-ins
Caddy notices an important change and texts you with a way to handle it. Reply to update the calendar, send the answer, or clear the next job.
The airline emailed a new departure time: 10:45am instead of 9:20. Your calendar still has the old time. Want me to update it?
Yes, update the flight event
Updated the departure to 10:45am and the arrival to 12:20pm, using the new local times in the airline’s email.
The problem
Important changes live across too many tools, so you often only notice them after the window to act has passed.
How Caddy helps
- Watch connected Gmail, Calendar, Slack, and Linear activity for meaningful changes.
- Deliver user-created reminders at the time you asked for them.
- Text a short explanation of what changed and why it matters.
- Suggest a useful next step while keeping sensitive actions behind approval.
Why Caddy is different
A useful check-in arrives at the right time, explains why it matters, and gives you a clear next step. You decide which sources Caddy can use, what deserves a text, and whether any sensitive action should happen.
What the workflow looks like
- 1
Connect the tools that hold the updates you care about or set a reminder in Messages.
- 2
Tell Caddy which people, changes, deadlines, or tasks deserve your attention.
- 3
Caddy texts when a matching update or scheduled reminder needs you.
- 4
Reply with what to do next and approve sensitive actions before they happen.
Texts to try
- “Text me when a booking email changes our travel plans.”
- “Let me know when a customer follow-up needs an answer.”
- “Update my flight event with the new times from that airline email.”
Common scenarios
Get a useful text before you ask
Caddy brings a reminder or connected-app change into the same iMessage thread where you already ask for help.
Related: AI assistant in iMessageKeep the bigger picture in view
Use a morning brief for the shape of the day and proactive check-ins for important changes that happen later.
Related: Daily briefCatch an important message
Tell Caddy which senders or topics matter so an urgent email can reach you without the rest of the inbox noise.
Related: Important email alerts by textBest ways to use it
- Start with a specific person, deadline, project, or reminder instead of every update.
- Tell Caddy when a check-in was not useful so you can narrow the rule.
- Disconnect a source or ask Caddy to stop proactive messages whenever you want less noise.
Frequently asked questions
What can trigger a proactive check-in?
A scheduled reminder or a meaningful change in a connected Gmail, Google Calendar, Slack, or Linear account can trigger a check-in.
Can I control which apps Caddy checks?
Yes. You choose which apps are connected and can disconnect them at any time.
Will proactive check-ins get noisy?
Start with specific people, projects, deadlines, or reminders. You can tell Caddy what was not useful and narrow the rule whenever you want.
Can I turn proactive messages off?
Yes. You can ask Caddy to stop proactive messages without removing the reminders and routines you created separately.
Will Caddy take action without asking?
Reply to ask Caddy to handle the update. It can make clear changes to your own calendar and asks before sending emails or invitations and placing orders.
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